1. Field of the Invention
This invention relates to certain halobenzene sulfonates and to flame retardant polymeric compositions containing these compounds.
2. Description of the Prior Art
During the past several years, a large number of flame retardants have been developed for use with an almost equally large number of flammable materials. Cellulosic materials such as paper and wood and polymeric materials such as synthetic fibers and bulkier plastic articles are just two examples of materials for which flame retardants have been developed. For any class of flammable materials, such as synthetic high polymers, those skilled in the art have long been aware that some flame retardant additives are more effective in some polymers than they are in others. In fact, many flame retardant additives which are highly effective in some polymer systems are virtually ineffective in other polymer systems, The mere fact, therefore, that certain compounds contain halogen and sulfur atoms does not assure that any given halogenated or sulfur containing compound will impart useful flame retardant characteristics to all or even to any polymeric systems. Furthermore, as those skilled in the art have improved the flame retardancy of polymeric materials, they have been simultaneously required to provide the necessary flame retardancy with a minimal effect upon other properties of the polymers such as their light stability, moldability and flexural, tensile and impact strengths. Balancing all of the foregoing considerations and thereby developing polymeric compositions with good flame retardant characteristics as well as a satisfactory balance of other properties is, consequently, a task which has in the past and presently continues to require the exercise of a high degree of inventive skill.
The prior art considered in connection with the preparation of this application in U.S. Pat. No. 2,412.116 to Baker, Jr., U.S. Pat. No. 2,412,117 to Baker, Jr., U.S. Pat. No. 2,485,095 to Harris et al., U.S. Pat. No. 2,486,417 to Jackson et al., U.S. Pat. No. 2,567,008 to Britton et al., U.S. Pat. No. 2,683,161 to Knowles et al., U.S. Pat. No. 2,894,971 to O'Rear et al., U.S. Pat. No. 3,021,944 to Buecheler et al., U.S. Pat. No. 2,962,514 to Carbon et al., U.S. Pat. No. 3,395,232 to White, U.S. Pat. No. 3,850,972 to Goralski, and U.S. Pat. No. 3,914,272 to Starks et al.
In particular U.S. Pat. No. 2,412,116 teaches phenyl sulfonyl diesters of nitro alcohols having the general formula ##STR1## wherein R is hydrogen or alkyl, Ar is a phenyl nucleus, and X is hydrogen, alkyl, and acylamino. These compounds are taught as plasticizers for synthetic rubber and similar type polymers.
U.S. Pat. No. 2,412,117 teaches phenyl sulfonyl triesters of nitro alcohols having the general formula ##STR2## wherein Ar is phenyl nucleus and X is hydrogen, alkyl and acylamino. These compounds are taught as being plasticizers for synthetic rubber and similar type polymers.
U.S. Pat. No. 2,485,095 teaches beta-monohaloethyl esters of manohalogenated benzene sulfonic acids having the formula ##STR3## wherein R is monohaloethyl. These compounds are disclosed as being useful as insecticides.
U.S. Pat. No. 2,486,417 teaches alkylbenzene sulfonic acid esters having the formula ##STR4## wherein R is an alkyl group containing 1 to 8 carbon atoms and A is an alkyl or aryl group derived from mono-and polyhydroxy acyclic and cyclic hydrocarbon compounds such as the normal acohols, the alkylene glycols, and the phenols and homologues thereof. These compounds are taught as being useful as plasticizers.
U.S. Pat. No. 2,894,971 teaches polyfluoroalkyl -p-toluenlsulfonates having the general formula ##STR5## wherein n is an integer from 3 to 10. These compounds are disclosed as being useful heat transfer fluids.
U.S. Pat. No. 3,914,272 discloses lower alkyl arylsulfonates having the formula ##STR6## wherein n is zero or one, R' is a halogen or a C.sub.1 to C.sub.4 alkyl group, and R" is a C.sub.1 to C.sub.4 alkyl group. These compounds are taught as being useful in a process for exchanging alkyl moieties between compounds comprising reacting lower alkyl arylsulfonates with a higher alkyl halide in the presence of an organic quaternary salt.
The compounds of the instant invention are better flame retardants and/or have greater thermal and/or hydrolytic stability than these prior art compounds.